The magic of High Maintenance, a web series on the cusp of its second—or first proper—season, is that it penetrates these fortresses, both door-shaped and ­human-shaped. The creation of married couple Katja Blichfeld (an Emmy-­winning casting director for 30 Rock) and Ben Sinclair (an actor and editor), the series debuted in late 2012 and released new installments over the following months. Its morsel-size ­episodes—each between five and 15 minutes long—and quick-twists-of-the-knife storytelling attracted a small but strong viewership, which attracted critics, who took up the kind of urgent championing that indie creators pray for. From the first season’s 13 snippets, all available for free on Vimeo, came a development deal with FX, attention from networks, and, finally, a chunk of cash from Vimeo to fund season two.

High Maintenance may also be the first indie web series that could plausibly launch its own genre. The premise of the show is simple: A weed dealer bikes around the city delivering to customers. As with emergency-room medicine and organized crime, the world of weed delivery lends itself beautifully to dramatization—there’s voyeurism, jargon, journeys across the spectrum of human need. Sinclair plays the nameless pot-dealing angel of mercy. Among the tokers introduced in season one are a cult member, a Helen Hunt–obsessed recluse, a cross-dressing dad (played by Downton Abbey’s Dan Stevens), and a traumatized stand-up comic (played by Hannibal Buress). Episodes can be nibbled à la carte or swallowed whole in one sitting. Together they add up to less than two hours.

When the Vimeo deal was announced in May, it represented the company’s first foray into original programming. Vimeo had already established a service where filmmakers could set a viewing price and take 90 percent of the proceeds; Kerry Trainor, the company’s CEO, says it was just a natural step toward advancing some money to High Maintenance, a show he thinks “shows off everything we think Vimeo is in the world to do.” For Blichfeld and Sinclair, who glued together season one of High Maintenance with their own funds and through favors from friends, it represented an ideal way to keep a good thing going. Vimeo has been an extremely hands-off partner: “That’s the coolest thing about being here,” Sinclair says. “They haven’t even read a single script. They haven’t asked.”

Blichfeld: “No one’s looking over our shoulder.”

Sinclair: “No one can tell on us.”

On an afternoon in August, the crew was staked out near a conference room at Vimeo’s Chelsea headquarters to film an office segment involving a martial-arts instructor. The nameless weed guy was performing a suite of ass-kicking moves on the instructor. Sinclair, who is wary-eyed and bearded, has a vocal slur that makes him sound three beers deep at all times and an intensity that he can flick on and off like a light switch. Blichfeld directed two takes of the scene (yelling, body-slamming) while 50 or so Vimeo employees typed quietly behind her, paying no mind. The atmosphere on-set was one of giddy and furtive productivity, as though the crew were trespassing and had to move quickly before the cops rolled in. (They also took heavy advantage of the tech-office snack bounty: Reese’s Peanut Butter Cups, a machine that dispenses every kind of soda.) Greg Clayman, Vimeo’s general manager of audience networks, occasionally wandered from his office to watch the action.

Blichfeld and Sinclair insist the cash injection hasn’t changed the couple’s process. They’re still working with actors whom they meet through mutual friends, like Orange Is the New Black’s Yael Stone, whom they met recently at a play. They’re still writing about topics that bubble up over dinner. (Upcoming episodes will have a heavier emphasis on career.) Sinclair had some mild concerns about editing episodes in an office, rather than at home in Ditmas Park, because he prefers to edit when “fucking stoned,” but he concluded that edibles would do the trick while at Vimeo.

What distinguished season one from the anarchy of indie web TV was its visual sheen and lean, reversal-laced plotlines. The episodes could have served as a launchpad for a conventional network show, sort of like how a short video Christmas card morphed into South Park on Comedy Central. ­Blichfeld and Sinclair went on a tour of studio meetings in L.A. last year, which led to a nine-month deal with FX to develop a 30-minute version of the show. Before writing any scripts, they pitched characters (Sinclair: “A shitload”), but the network consistently gravitated toward the more recognizable stock characters. It didn’t pan out. There were other potential homes, too, like Comedy Central, but as Blichfeld puts it, “We were like, ‘Oh, shit, they’re gonna want an episode full of jokes every week when sometimes we want to do an episode about a sad shut-in that isn’t actually laugh-out-loud-funny.’ ” In the end, Vimeo’s offer won them over. Even though the deal only fronts the production costs of six episodes, they hope that charging viewers an as-yet-undetermined price for each episode will create a healthy revenue stream.

And staying indie, at any rate, will allow the show to keep doing what it does well: showcasing undervalued actors, lollygagging in corners of Brooklyn, and chronicling the everyday indignities that city dwellers—not just New Yorkers—endure. Like the houseguest who leaves a pair of filthy Q-tips on the bathroom counter, or those freaks who walk among us clipping their fingernails on the subway. “Katja’s model public citizen is Danish,” Sinclair explains. “Quiet, respectful. Hygienic. Almost anything in New York violates one of those rules.”

Also technically verboten in New York: weed. But there’s nothing shady about Sinclair’s dealer, who has all the emotional intelligence of a gifted therapist and, like any good salesman, remembers flattering details about his clients (“Where’s your lady friend, man? That redhead?”). When the new season debuts in early November, ­Blichfeld and Sinclair will find out whether their own customers mind paying for something they used to get for free—whether those first beloved episodes, maybe, were exactly the right gateway drug.

*This article appears in the September 22, 2014 issue of New York Magazine.

A New Yorker’s apartment is his kingdom, but for many of us, it’s a solitary domain. Inviting someone into your home forces you to gaze upon it with fresh eyes, and it inevitably looks squalid: too small, too dark, shabbily decorated, oddly shaped, and weird-smelling. The default solution is to socialize externally and keep the front door closed. I can count on two hands the number of friends who’ve stepped inside my fifth-floor walk-up, and I’d sooner cry in public than ask a neighbor in for coffee.

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